Fairfield, CT Homes for Sale with Acreage

Greenfield Hill proposed new construction on a 2.65-acre lot along a Town-designated Scenic Road, to be built by award-winning design-builder Bonnie Paige in collaboration with Vicente Burin Architects. The proposed residence is based on a design sold in Southport Village; interested buyers may tour similar homes and meet the team to tailor plans, finishes, and timeline. The property sits among

Andrew Whiteley Brown Harris Stevens

Enchanting countrystyle retreat offering the warmth of a welcoming neighborhood with the luxury of natural privacy, nestled amid professionally landscaped gardens and mature trees. Designed for gracious living and effortless entertaining, 165 Hemlock Hills S blends refined upgrades with modern comfort throughout. Featuring two primary suites, five bedrooms, and four beautifully renovated baths,

Lois Lehman William Raveis Real Estate

Sasco Point- A Rare Waterfront Estate. Perched on over 11 acres with 450 feet directly on Long Island Sound, Sasco Point is an extraordinary coastal retreat. Nestled at the end of prestigious Sasco Hill Road, this architecturally stunning estate blends Swedish, Dutch, and Moorish influences, creating a residence that is as elegant as it is timeless. A discreet gated entrance leads to a winding

Andrew Whiteley Brown Harris Stevens

New Construction of a farm house style colonial in the prestigious Greenfield Hill section of Fairfield. Approvals in place for this home on a designated scenic road. 193 feet of frontage plus city water available in the street. This is an excellent opportunity to customize your dream home on a beautiful, cleared and leveled Greenfield Hill lot surrounded by nature, charming New England stone

Mona Cascella William Raveis Real Estate

Set within The Ridge in Greenfield Hill, Fairfield's gated residential community, this residence originally designed by renowned architect Bill Blanski has been completely rebuilt and thoughtfully reimagined with the scale and finish of new construction. Spanning over 7,500 square feet, the home offers four bedrooms and six full and two half baths, with wide plank oak floors, multiple fireplaces,

Erin Melson The Agency

The Ultimate East Coast Sanctuary-Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is engineered for the world's most discerning icons who demand seclusion with proximity to NYC. This 38.91-acre compound ,is the mid century former home of Richard Rodgers, composer of The Sound of Music. Restored and expanded to incorporate 7 bedrooms and 7

Leslie Razook William Pitt Sotheby's Int'l

Nestled on a picturesque cul-de-sac street in the heart of Southport, 70 Meadow Ridge Rd offers the perfect blend of classic charm and modern convenience. This custom home boasts 6 bedrooms and 5, Bathrooms providing ample space for comfortable living and entertaining. Step inside to discover sun-drenched living spaces featuring gleaming hardwood floors, a cozy fireplace, and an open-concept

David Krasnoff Compass Connecticut, LLC

3808 Redding Road is the kind of property that feels discovered rather than found. A place where time has softened the edges, and the landscape tells its own story. Dating to 1769 and set on nearly eighteen acres of open fields and mature trees, this is one of Fairfield's earliest homes, thoughtfully rebuilt in 2008 to preserve its character with modern ease. Inside, the home unfolds with warmth

Cindy Raney Coldwell Banker Realty

Eight minutes from downtown Westport, escape to 11 Judges Hollow-a 1930's rustic hunting cabin on 1.6 private wooded acres at the end of a long secluded driveway. A one of a kind private in holding completely surrounded by the 180 acre Brett Woods Conservation Area, this rare property offers ultimate privacy with protected open space as your permanent neighbor. Judges Hollow is nestled within

Lisa Hartmann William Pitt Sotheby's Int'l

In the heart of Greenfield Hill proper at the top of Bronson Road, this special and truly unique estate presents a rare opportunity in one of Fairfield's most coveted locations. Set on just over two acres of beautifully landscaped, professionally photographed grounds, the property reflects a timeless elegance that would be costly to replicate today. Across from a distinguished equestrian family

Tara Hawley Coldwell Banker Realty

Embrace the tranquility of this exceptional equestrian estate, nestled on 4.45 acres of private beautiful land. This serene property is a haven for horse and animal lovers, featuring expansive pastures, barn, stable, shed, paddocks and sand riding ring. This one-of-a-kind property borders the Aspetuck Land Trust, offering unmatched natural beauty and privacy. The renovated and well-maintained

Ellen Fusco Compass Connecticut, LLC

A special property with pool & tennis court, on the Westport border, minutes to shops, restaurants and train. Experience refined luxury in this picturesque setting, situated back from the road down a long, lighted driveway, winding past a serene pond. Nearly 4000 sq ft with 4 bedrooms & 4.5 baths, this open floor plan home features city water, sewer, natural gas, oil heat and central A/C for

Mary Ellen Gallagher Compass Connecticut, LLC

Set within artisan stone walls with curated flowering landscapes, this magnificent stone and stucco residence is a masterful tribute to Southport's enduring architectural legacy. Designed to blend seamlessly among the grand neighboring estates of this coveted enclave, 688 Hulls Farm strikes a rare balance: modern in execution, timeless in presence. Construction begins in April with Coastal Luxury

Jaclyn Picarillo Higgins Group Bedford Square

Rolling Hills Drive is the kind of street where homes feel settled into their surroundings, quiet and residential, with attractive homes lining the neighborhood and nature close at hand. Just moments from hiking trails, Lake Mohegan, and Smith Richardson Golf Course, it's a setting that offers both neighborhood connection and easy access to the outdoors. At 126, a classic Colonial sits gracefully

Cindy Raney Coldwell Banker Realty

Welcome to 96 Toll House Lane, set on well over an acre in one of Fairfield's most beloved neighborhoods-where people move in and stay. At the heart of it all is Dover Park, offering a true sense of community with its playground, ball field, and open green space. Inside, the home offers easy, everyday living with an open flow between the living room and eat-in kitchen-ideal for both daily life

Clyde Wauchope Coldwell Banker Realty

Tucked away in a prime Easton location that feels worlds apart - but still connected - this effortlessly cool mid-century home captures the ultimate California vibe. With four bedrooms, three full baths, one half bath, and an office, the layout blends timeless design with everyday functionality. Clean architectural lines, expansive windows, and seamless indoor-outdoor flow fill the home with

Lisa Holler Compass Connecticut, LLC

Welcome to this beautifully, renovated colonial, nestled in a quiet cul-de-sac in desirable Easton, Connecticut. Set on nearly 2 acres of professionally landscape property, this charming, four bedroom home offers the perfect blend of privacy, comfort, and classic New England character. Inside, you'll find spacious living areas filled with natural light, including a stunning family room featuring

Jeanne Hurty Brown Harris Stevens

Design Your Dream Home with an Award-Winning Builder. Step into a world of elegance and sophistication with a soon-to-be-built 6,660 sq. ft. masterpiece by Coastal Luxury Homes. Known for their innovative designs, sleek modern lines, and unparalleled craftsmanship, Coastal Luxury Homes has earned a reputation for creating some of the most sought-after residences. With a focus on prime location,

Annie Klyver Higgins Group Real Estate